


The Contract Stipulation

by TQMZ



Category: Highschool DxD (Anime)
Genre: Anal Sex, Blow Jobs, Explicit Sexual Content, F/M, First Kiss, Marriage Contracts, Oral Sex
Language: English
Status: In-Progress
Published: 2020-12-15
Updated: 2020-12-15
Packaged: 2021-03-11 00:33:38
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,115
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28086243
Author URL: https://archiveofourown.org/users/TQMZ/pseuds/TQMZ
Summary: Rias should have gone straight to Issei and tried giving him her purity before the wedding. Instead, Riser showed up before she could leave... (Smut!)
Relationships: Rias Gremory/Riser Phenex
Comments: 2
Kudos: 16





	The Contract Stipulation

**I don't own anything!**

Commissioned by Anonymous.

**XxXxXxX**

"Going to see the brat, Rias?"

Rias Gremory, a beautiful red-haired girl with a killer body, about to enter adulthood, froze. The sound of Riser's voice behind her feeling like ice in her veins. Slowly turning around, Rias saw her fiance, Riser Phenex, laying on her bed, having gone entirely unnoticed by Rias as she changed and got ready to see her pawn. "W-When did you g-get here, Riser?"

A charming smile on his face, Riser slowly stood up and walked over to Rias. "Oh, nothing much a... _Friend_ of mine recently told me how you want to escape the wedding... by losing your virginity to a commoner of all people."

Her face now losing color, Rias stayed still, not wanting to agitate Riser more than he already was. Despite wanting to escape their marriage, Rias had at one time years ago tried to like Riser, learning everything she could about him. One of those things she learned was that the more calm Riser was, the more fury he was hiding behind his charming facade. Fury Rias could see burning in the eyes of the man in front of her.

Chuckling, Riser trailed a finger across Rias's collarbone, making the girl tremble. "Nothing to say, Rias?"

"I-I-" Rias stuttered, trying to think of something, anything to say that would get her out of this predicament. However, Riser didn't let her, cutting Rias off.

"You know, I really thought you would change your mind. Everyone told me you would, so I gave you multiple chances after chances." Riser paused, then looked in Rias's eyes. "I even held back from coming here when I heard you slept naked with one of your pieces."

If Rias had paled before, she was ghostly now. Scared at what Riser was going to do and horrified to learn she been monitored all this time without her knowledge. Rias had thought staying in the human world would keep her safe from Riser, not allow him to have eyes on her more easily than he could have in the underworld.

"But now, you wanting to sleep with a commoner, a piece of trash just to escape our marriage." Riser's smile turned a little twisted. "It losses me off, it pisses me off so much that I've decided to take what's mine. Well, be married tomorrow anyway. It won't make much difference."

"Y-You can't... Y-You can't do that." Rias stuttered, taking a few steps back, her eyes involuntarily flickering down to Riser's pants.

"Oh, and who gave you that idea?" Riser asked now, looking amused, having noticed Rias's glance. "Have you ever read our marriage contract? More specifically, the stipulations at the bottom of the third page?"

Hesitantly Rias thought back to when their marriage was arranged years ago and realized she'd never bothered to look at the contract, let alone read it.

"Let me enlighten you then. At the bottom of the third page, theirs a few little sentences that explain how fickle youth can be, constantly changing their minds..." Riser paused then grinned, a grin that worried Rias more and more as Riser continued to talk. "It also says that to prevent such an occurrence, at the age of seventeen, the two contracted devils can be intimate. A way to help develop the relationship if you will."

"NO!" Rias cried out, shaking her head. "Onii-Sama wouldn't-"

"He doesn't know." Riser interrupted, looking smug. "It was our fathers who negotiated the contract, and as you know, your father wouldn't care. He has a harem of his own. I doubt he even noticed what the stipulation meant when it was added."

"Y-You bastard!" Rias glared, not wanting to acknowledge it but knowing such a thing was possible with her father.

"Of course, I won't force you. You can walk away if you so desire." Riser nodded to the door on the other side of the room, strangely out of character for the arrogant devil, getting Rias nervous.

"What's the catch?"

Riser put a hand an exaggerated hand on his chest, looking offended. "Catch? Why, Rias, I'm hurt. There's no catch at all, Either I fuck you today or tomorrow after our wedding. No matter what, I win."

Clenching her fist, Rias glared hatefully at Riser and headed for the door, thoroughly planning on walking out and going back home to the underworld to see her brother and see if he would finally change his mind about the contract. However, just when Rias was about to turn the doorknob, she realized a keyword Riser had used as he talked. "...What do you mean by stipulation?"

"You did notice." A smile flashed across Riser's face. "It looks like your not as foolish as I first thought. I suppose that's a good thing. Can't have my wife shaming the Phenex name."

"Answer the question!" Rias ground out, momentarily forgetting the fear and terror she had felt not even a minute prior.

"Well, as you know, before your brother became satan, the war had drained most of the Gremory's resources. So unlike now, with how much gold your family has accumulated over the years. It was simple for your father to agree at the time that he would hand over whatever fortune was left if any stipulation was broken."

"What?" Rias frowned, racking her brain for what Riser was talking about. She'd never heard of this before. To the best of her knowledge, her family had always been a noble and wealthy one.

Riser shrugged uncaringly, sitting down on Rias's bed once again. "Keep in mind it was before you were born, Rias. I wouldn't be surprised if they were too embarrassed to tell you."

For a second, Rias imagined vanishing Riser with the power of destruction, her power welling up in her body. But she cut off that thought, her power dying back down, knowing Riser would regenerate, and it would do nothing but get him angry.

"If I refuse." Rias started, looking at Riser. "Then we marry tomorrow, and you get the phenex fortune."

"I'm thinking of buying an island, just for the two of us." Riser tapped his chin. "What do you think?"

Holding back a scream, Rias was about to teleport out and froze. Realization of what Riser was doing hit her.

_He wants me to leave... He can have as much sex as he likes with any of his harem. So why would he do this, unless he knew I wouldn't have sex with him... allowing him to get the Gremory fortune..._

Taking a deep breath and knowing what she was about to do was everything she had fought against all these years. Rias smiled, then got on her knees in front of Riser, unbuttoning her shirt as she did so.

"Rias?"

Smile widening, Rias saw the way Riser's eyes watched her, no doubt surprised she was willing even to consider doing this. _I knew it. I was right._

"Hahaha." Riser laughed, watching as Rias stripped off her button-up, her naked tits exposed to the cold air of the bedroom. "No bra, as expected of an exhibitionist."

Rias glared up at the man, her cheeks heating up, but ultimately she said nothing, wanting to get this over with as quickly as possible.

_For the Gregory fortune, for the gremory fortune._ Rias chanted in her mind, her hand shakily moving forward and unzipping Riser's pants. His cock slowly rising out of its cage, still soft as it slanted over.

_Why isn't it hard?_ Rias thought, frowning, a little insulted. Back at Kuoh, her merely walking down the hall in her school uniform made the boys get bulges. But to have Riser not even be hard with her kneeling, her head right next to his cock was infuriating.

"Are you going to watch or get on with it?" Riser asked, sounding bored, making Rias have doubts about her body for the first time.

Shaking her head, Rias closed her eyes, taking a deep breath as she gathered her courage. Then leaned forward, pressing her mouth against Riser's cock.

Unknown to Rias, Riser watched this all with amusement dancing in his eyes. His cock hardening against the girl's lips, causing Rias to open her eyes in shock.

_How is he this large!_ Rias pulled her head back, dumbfounded as Riser's cock grew larger and larger, easily beating Issei's, who Rias had caught a glance of during their training trip.

"Surprised?" Riser smirked, Rias's reaction being something he had gotten from women many times over the years.

"S-Shut up!" Rias stuttered, looking away, a suspicious blush on her face.

_I can't be attracted to him, right? Damn my body and its reactions._ Rias thought, annoyed, shifting her legs a little.

Something Rias had failed to explain when telling Issei about devils. Was that every devil had a sin, Issei for example, obviously had lust as his. However, for Rias, her sin or rather sins was special. Instead of one or two, she had all of them, with greed and lust being the strongest. Now half-naked and with the stench of Riser's cock filling her nostrils, Rias could feel her desire building up in her, the sin growing stronger every second as she felt a cock for the first time.

"Why don't you give it a lick." Riser frowned, growing a little impatient at the dazed Rias. He knew his size was large, but sitting there watching it shocked, without doing anything, was ridiculous.

Rias, not knowing Riser's thoughts, hesitated, then tentatively gave the cock a lick. Eyes widening, she paused then gave another lick, surprised at the almost nonexistent taste, and what she could taste wasn't bad.

_I thought it was supposed to be horrible, with me choking..._ Rias sighed inside, making a mental note to delete the lying hentai in her collection. It definitely wasn't like it was in the anime. Speed increasing, Rias slowly covered Riser's cock with her spit, her chin now wet from all the excess saliva sliding off of Riser's cock.

"It's wet enough. Use your tits now." Riser ordered, and surprisingly Rias listened without saying a word, her mind getting more and more cloudy, unable to think as clearly as she could a few minutes before.

Lifting her breasts with her palms, Rias pressed them against Riser's cock, shivering at the wet feeling on her tits, her nipples hardening as her body grew hotter. Moving closer, Rias wrapped them around Riser's cock, the smell getting her lightheaded as she breathed.

"That's it." Rias heard Riser's smooth voice cut in through the fog in her mind. "Now lift your tits, then bring them back down again."

Obeying, Rias pressed her breasts against Riser's cock, bringing them up and down, forming a seal around it, a few gasps escaping her lips as her body heated with arousal. Amazingly, however, even Rias's large breasts couldn't completely swallow Riser's cock. The tip and a good part below it still visible as Rias gave him her first titfuck.

"A little faster... Perfect." Riser groaned, his cock almost throbbing at the softness of his fiance's breasts. That and the knowledge that he had the ever prideful Rias Gremory on her knees giving him a titfuck was almost enough to send him over the edge. _Almost_ , thankfully he had plenty of experience and could hold back if needed.

The wet squelching sound of her tits knocking together as she slid them up and down Riser's cock echoed in Rias's ears. Momentarily focusing, she stared down at the hard cock just below her chin. _Why... Why is this taking so long? When is he going to cum?_

Not stopping the titfuck, and without any orders from Riser, Rias slowly descended her head and gave the head of Riser's cock a small lick, her spit trailing down and disappearing in between the valley her breasts. _Maybe he'll cum faster this way._

"You're full of surprised, aren't you, Rias." Riser's chuckled, his eyes lighting up as the girl continued to lick at his cock, looking in no way the proper pureblood devil she was. Instead, she looked more like a teenage slut with all the sweat sliding down her voluptuous body, her tongue concentrating on the task before her. "I should have done this the day you turned seventeen."

"Mmm..." Ross moaned into Riser's cock at the devil's words, her imagination flying.

"Oh?" Riser's raised an eyebrow, playing with a few strands of Rias's hair. "Do you like that idea? Does the thought of me claiming you turn you on Rias?"

Rias stayed silent, not answering Riser's question. However, she didn't need to. They both knew she was enjoying what was happening between them far more than she should. At least she was if the trembling of her body and the way her legs clenched as Riser spoke was any indication.

"Look at me." Riser said after a few minutes, his voice sounding a little more strained than it had before, the slight twitch of his cock showing he was soon approaching his limit. However, Rias being the virgin she was, didn't realize this and took her mouth off of Riser's cock to look up at him, not stopping her hands from moving her breasts around the cock between them.

"Fuck!" Riser groaned. The sight of Rias with his cock between her shiny spit covered tits, looking up at him with blushing cheeks, was even better than he had imagined it would be. A second later and Riser was shooting his cum all over Rias's tits, with a few spurts hitting her chin and lips, covering the girl in his seed.

Her lust now fully taking over, Rias licked her lips clean, then started scooping up Riser's cum from her breasts and into her mouth, not letting a single drop go to waste, her taste buds exploding at the flavor of Riser's cum.

_She's mine now._ Riser thought possessively, loving the way Rias looked with his seed coating her body. Standing up, his cock less than an inch in front of Rias's face, he began his next order. "Clea-"

Before Riser could even fully say what he wanted, Rias swallowed down his cock, deepthroating his cock in a single go. Something Riser hadn't thought was possible, not even the women in his harem had managed it on the first try.

After a few minutes of enjoying the feeling of Rias's throat around his cock, Riser pulled out and sat back down on the bed, his cock fully hard once again, his phenex regeneration ensuring he would be able to keep going as long as he wanted.

"On the bed, now." Riser told Rias, smirking as she did exactly as he asked, a small puddle of her arousal on the floor where she'd been kneeling. Grabbing the edge of Rias's skirt, Riser pulled it off, making sure to take the time to palm the female devil's arse in front of him as he did so.

In some part of Rias's mind, a part that still hadn't fully succumbed to her lust, she hesitated. Once she took this last step, there would be no turning back, and nothing she did would be able to change that... Unfortunately for Rias, Riser didn't give her any more time to think. Instead, he lifted Rias with a single arm and captured her lips in a kiss.

Rias's eyes widened, realizing she just lost her first kiss. Then feeling Riser's tongue against her lips, Rias closed her eyes in resignation and opened her mouth, allowing his tongue access to hers.

"You stole my first kiss," Rias whispered shakily, her eyes locked on Riser's lips, feeling the strange desire to kiss them again, feeling their softness.

"Then I better make sure you remember it." Riser smiled, a smug look entering his eyes before leaning down, capturing Rias's lips once again.

Ten minutes later and with many many kisses in between, Rias finally fell back with a large gasp, her cheat heaving as she got her breath back, her swollen lips the only evidence of what the two had been doing all this time.

Smirking, Riser lifted Rias's legs and pushed them back until they were almost touching the bed beside Rias's head. "Time for the main event, princess."

Rubbing his cock against the female devils' pussy, Riser lubed up his cock, getting it wet with Rias's arousal. Smirking lustfully, Riser looked down, admiring the view of the Gremory princess beneath him, the sight of her sweaty hair spread out on the bed, and her naked body wet and ready for him burning into his mind. A memory Riser was sure he'd never forget.

"That should be enough." Riser murmured, then to the confusion of Rias, he pulled away, not penetrating her at all. A moment later, her confusion was gone and replaced with fear as she felt Riser press the head of his cock against her arse.

"What are you-AAAAHHHHH!" Rias screamed in pain, Riser having shoved the entirety of his cock up her arse, making Rias feel as if he was splitting her in half.

Groaning, Riser felt as if his cock was getting crushed. The feel of Rias's arse closing like a vice, keeping him locked inside her, unable to pull out. Annoyed now, Riser slammed his lips down on Rias's, kissing her roughly, stopping her screaming. After a few minutes, he pulled away, leaving Rias gasping for breath. "Relax, Rias. You'll feel better if you do."

"Mhm..." Ross whimpered but did as Riser suggested, relaxing her arse muscles as much as she could. Sure enough, within a minute, Rias felt the pain start to dissipate, the feeling of having a cock in her arse little more than discomfort.

Riser breathed a small sigh of relief as he felt Rias relax, the crushing feeling disappearing, leaving only the tight feel of Rias's walls. A much better sensation compared to before, Rias love anal sex as much as the next devil, but getting his cock crushed into pulp was not something he enjoyed, even with his level of regeneration being what it is.

Gently pulling out part of his cock, Riser let Rias adjust, then slowly pushed himself back in, causing a wince of pain to flash across the female devil's face. "You're doing wonderful, princess."

A feeling of pride came over Rias, the sin showing up for the first time since this who mess had started, overpowering her lust for a second. _Why do I feel happy hearing those words?_

"Ughhh..." Rias moaned quietly as Riser gave a short thrust, a pleasurable feeling welling up in her for the first time, letting her easily ignore the slight twinges of pain that she still felt. "Faster~."

Smiling, Riser decided to do as Rias asked, just this one time as he wanted to pick up the speed as well. Pushing Rias's legs back with his hand's Riser used them to keep his balance, then he slammed his cock down into Rias's arse, her warm, tight walls clenching around him, barely letting him slide through.

"Yess..." Rias mewled, arching her arse a little, trying the best she could to allow Riser better access into her arse. "Fuck me harder, Riser."

Keeping a steady rhythm, Riser slowly increased the pace of his thrusts, increasing the speed, causing a loud slapping sound to echo throughout the room as their hips slapped together.

"Fuck, fuck, fuuuck!" Rias chanted, her eyes half-closed as the pleasure started to overwhelm her mind. The feel of Riser's cock in her arse almost bringing her over the edge without any stimulation besides what was currently in her arse.

Noticing this, Riser halted for a second, then began to laugh, the speed and strength of his thrusts increasing as he continued to fuck Rias. "I never took you for an anal slut, but I suppose there are a lot of things I never expected you to enjoy."

"I-I'm not a slut." Rias choked out, the moan she let out right after those words not helping her case.

"Is that so." Riser slowed down, almost coming to a complete halt. "Then you'll be fine if we stop and continue this tomorrow..."

"NO!" Rias gasped, clenching around the cock inside her, eyes quickly finding Risers. "I'll be a slut if you want, just don't pull out!"

"Very well." Riser said before resuming the speed he was at before. "Remember those words when this is over."

While confused as to why Riser said that, Rias didn't let it bother her, Instead concentrating on the waves of pleasure crashing through her, is set, her marriage to Riser, and even what she had planned to do tonight long forgotten as she was fucked by the devil above her.

"If I knew you were this tight, I would have seduced you long ago, " Riser growled hungrily, giving Rias's arse cheek a small slap, resulting in a bright red mark appearing on her skin. "Of course, if I did, doing this now wouldn't be near as fun."

Despite herself, Rias couldn't help but agree with him, the devil inside her loving the way Riser dominated her body. With a small part of herself wishing she had agreed to the marriage earlier, maybe even offering her arse to Riser so she could feel the pleasurable high she was feeling now.

"Fuck I'm getting close. Where do you want it?" Riser asked after a few moments, giving Rias a choice. Something that both surprised and excited the young female devil.

However, it was a choice Rias didn't need to think much about. She knew exactly where she wanted Riser's seed. "Inside. Fill up my arse!"

"Gladly."

As soon as Rias felt the first shot of Riser's cum fire into her arse, she felt as if her mind exploded. Pleasure beyond anything she had felt before flooded her mind, her pussy tingling, while something wet poured down her arse.

"Haha!" Riser laughed as he watched Rias cum for the first time that night, her pussy spraying out a bit of her arousal before sliding down her arse and mixing with his cum, her arse unable to keep his entire load inside, letting some escape, white droplets dripping out onto the bed staining it. "You'll be a wonderful addition to my collection!"

Eyes refocusing, Rias gazed at Riser, then glanced down at the cock still in her arse. Shame and mortification filling Rias's mind as she realized what happened and that she had cum with no one touching her pussy at all. _It's like something out of my hentai anime._

Pulling out of Rias's arse, Riser released one last spurt of cum, the white liquid shooting onto Rias's stomach, completing the picture.

Seeing him finish, Rias frowned, feeling relief that it was over, but also no small amount of disappointment. _We're not done, are we? He still hasn't taken my virginity._

"If you're this good now, I can't wait until we're married and more experienced." Riser chuckled, putting his suit back on his body.

"Why... Are you finished?" Rias glanced down, her body still trembling, the orgasm having removed a lot of the heat inside, but she was still horny and wanting to continue.

"I would love to go further, Rias, but that would violate the contract. And I can't have that... I'm sure you can hold up until tomorrow night."

Rias blinked, a cold sick feeling entering her gut, extinguishing the heat that was just building up. "...What did you say?"

"You didn't truly think I was telling you the truth, did you? With how protective Sirzech is, there's no way he would have let such a stipulation exist."

"B-But..." Rias trailed off her mind in chaos as she listened to Riser speak.

Amused, Riser grinned down at the confused Rias, his hand stroking her red hair. Surprisingly she didn't slap it away, even with the information he'd revealed. "As your magic seal isn't on your mouth or arse, using those two holes won't register, and therefore don't count as sex. Keeping the contract valid."

"You bastard." Rias glared, the effect significantly reduced as she was naked and covered in both of their fluids.

Shrugging, Riser activated his teleportation circle, then gave Rias a little wave. "See you at the wedding."

All was silent for the next few minutes, then ever so slowly, Rias sat up and trailed a hand down to her legs, picking up some excess cum that had slipped out. Staring at it, Rias hesitated for a moment, then took her finger in her mouth, her tongue swirling around it, memorizing the taste as she cleaned it before swallowing.

"Maybe marrying him won't be so bad,"

**XxXxXxX**


End file.
